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Thiazolyl aminobenzoic acid derivative and application thereof

An alkyl and methyl technology, applied in the field of preparation of thiazole aminobenzoic acid derivatives, can solve problems such as inability to effectively solve drug resistance, and achieve the effects of solving drug resistance problems, inhibiting cancer cells, and improving the strength of action

Active Publication Date: 2019-01-18
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with imatinib, it can solve the drug resistance caused by most mutants, but it cannot effectively solve the drug resistance caused by the T315I mutation (Ann Oncol, 2007, 18 (6): 42-46; Eur J Cancer, 2010 , 46 (10): 1781-1789; Haematologica, 2014, 99(7): 1191-1196)

Method used

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  • Thiazolyl aminobenzoic acid derivative and application thereof
  • Thiazolyl aminobenzoic acid derivative and application thereof
  • Thiazolyl aminobenzoic acid derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 3-[(5-Ethyl-4-phenylthiazol-2-yl)amino]benzoic acid

[0046] Step a:

[0047]

[0048] Add 11.4341 g (0.12 mol) of ammonium thiocyanate and 20 mL of acetone into a 100 mL oblique-necked reaction flask equipped with mechanical stirring and a condenser, and stir evenly through mechanical stirring. 16.8034 g (0.13 mol) of benzoyl chloride was added dropwise (dropped in 10 min), and the solution changed from clear to white turbid. Heat to reflux, add 14.1147 g (0.10 mol) m-aminobenzoic acid in 4 batches, monitor the reaction process by TLC (ethyl acetate:petroleum ether = 4:1), and complete the reaction in 8 h. Cool, filter, and dry the obtained solid to obtain 28.0041 g of light yellow powder 3-(3-benzoylthioureido)benzoic acid, m.p. 184 ~ 186 ℃.

[0049] Add 0.9913 g (0.12 mol) of 3-(3-benzoylthioureido)benzoic acid and 33 mL of 10% NaOH into a 100 mL oblique-necked reaction flask with a condenser, the measured pH=13, magnetic stirring, and heating Reflux,...

Embodiment 2

[0053] Example 2 3-[(5-methyl-4-(4-methylaryl)thiazol-2-yl)amino]benzoic acid

[0054]

[0055] The operation was the same as in Example 1, and 2.4358 g of dark green crystals were weighed, with a yield of 57.72%, m.p. 257-258 °C. 1 H NMR (DMSO-D 6 , 400 MHz), δ : 2.35 (s, 3H, CH 3 ), 2.42 (s, 3H, CH 3 ), 7.27-8.27 (m, 8H, 2×C 6 h 4 ), 10.42 (s, 1H, COOH).

Embodiment 3

[0056] Example 3 3-[(4-(4-chlorophenyl)-5-methylthiazol-2-yl)amino]benzoic acid

[0057]

[0058] The operation was the same as that in Example 1 to obtain 4.5789 g of brown powder with a yield of 54.19%, m.p. 257-258°C. 1 HNMR (DMSO-D 6 , 400 MHz), δ : 2.44 (s, 3H, CH 3 ), 7.44-8.27 (m, 8H, 2×C 6 h 4 ), 10.40 (s, 1H, COOH).

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PUM

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Abstract

The invention discloses a thiazolyl aminobenzoic acid derivative with antineoplastic activity, which can be used for preparing an anticancer drug, in particular as a Bcr-Abl tyrosine kinase inhibitor,especially as a Bcr-Abl tyrosine kinase inhibitor of a T315I mutation.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a series of thiazole aminobenzoic acid derivatives, their preparation methods and uses. Background technique [0002] Chronic myeloid leukemia (CML) is a malignant myeloproliferative disease originating from hematopoietic stem cells, accounting for 15%-20% of all leukemias, and is the most common myeloproliferative disease. The root cause of the disease is the Bcr-Abl gene formed by the fusion of the proto-oncogene c-Abl on chromosome 9 and the Bcr gene on chromosome 22. At present, it has been confirmed that Bcr-Abl tyrosine kinase is the most ideal molecular target for the treatment of CML (Blood, 1996, 87: 3036-3038; Blood, 2000, 96: 343-356). Around the Bcr-Abl tyrosine kinase, pharmaceutical workers have made various efforts. At present, the successfully marketed Bcr-Abl tyrosine kinase inhibitors include imatinib, nilotinib, radotinib, dasatinib, subotinib and ponatinib...

Claims

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Application Information

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IPC IPC(8): C07D277/42A61K31/426A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07D277/42
Inventor 彭俊梅刘娟黄红林谢志忠曹轩赵琼兰姜玲徐诗宇
Owner NANHUA UNIV
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